


Love and Pain

by Deansimpallagrl



Series: Love and Pain [1]
Category: Supernatural
Genre: Anal Fingering, Anal Fisting, Anal Plug, Anal Sex, BDSM, Blow Jobs, Bottom Sam Winchester, Breathplay, Canes, Cock Cages, Cock Rings, Come Eating, Demon Deals, Demon Dean Winchester, Demons, Dildos, Hair-pulling, Handcuffs, Hell, M/M, Minor Violence, Shock, Top Dean Winchester, Wax Play, Whipping
Language: English
Status: Completed
Published: 2019-01-28
Updated: 2019-02-02
Packaged: 2019-10-18 01:47:47
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 9,804
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17571977
Author URL: https://archiveofourown.org/users/Deansimpallagrl/pseuds/Deansimpallagrl
Summary: Sam is trying to do the unthinkable.  He must be with Dean even if he is a Demon.  Will Sam be able to go through with his plan?  Can Dean still love?





	1. Demon Deal

**Notes for the Chapter:**

> This is a little dark just to warn you

Dean sitting in his chair stares into the firelight. His thoughts are on Sam chained to the wall. He grins as he hears muffled cursing and the sound of chains jingling. His little fuck boy is so full of his cum and it seems he needs some more. His grin gets wider as he remembers how this happened. The mark of Cain turned him into a demon, and when he refused to get rid of it, Sam decided he would rather be with Dean than out in the cold. Sam made a deal to become the only thing that could let him stay with Dean forever, a demon. 

Crowley chuckled when he heard Sam’s request.

“Are you nuts moose? Why would you want this?” Crowley knew the answer, but he wanted Sam to squirm.

“You know why, you asshole. You made him into a demon. If that mark is there, I can’t have him back. So now I can be like him and still have him. It isn’t my first choice, but I love him.” Sam balls his fists and looks away. He wants so badly to break Crowley’s nose because this is his fault. He needs this to happen, so he just holds back the anger.

“Calm down now. Your old pal Crowley is here to help. The trouble is we need to demonize your soul. You wouldn’t want some other demon possessing you. So maybe we can kill two birds with one stone. If we let Dean do the torture maybe, we can get you there in less time. He does know you best.” Crowley’s eyes are sparkling as he watches Sam’s face. He never imagined the mark might take out the two top hunters. He just wanted Abbadon gone and Dean distracted. Now he might be able to keep them both out of the action long enough to gain some traction again in hell.

“What do you want from me? I am obviously keeping my soul so what do you want?” This is the tricky part. He doesn’t want to leave Dean’s side, but Crowley is always ahead of the game. Sam watches with a blank face.

“I need to make sure that Dean is on my side. He is powerful and I might need him again in the future. With you to keep him occupied he should be loyal. He is also bad for business. Is it a deal?” Crowley wants Dean out of sight so he can get back to his old reputation. Using Dean as a sidekick backfired and he wants the embarrassment out of sight. This way Dean will be so busy he won’t bother anyone else.

“Yes and no tongue.” Sam shivers because Crowley makes his skin crawl. He leans in and gets a hard and painful kiss. He jerks back almost growling.

“Your no fun. I set up a space for Dean in Hell. I will take you then you two can work out the rest. Remember moose, he needs to focus on you. “ Crowley’s grin makes Sam uneasy but he nods as Crowley snaps his fingers. They appear in a large stone room with an enormous fireplace. There is a chair, a bed and not much else. The floor is littered with garbage and clothing. Some clothes cover the large bed. There are no other things on the walls. A blood red carpet is on the floor leading from the door towards the fireplace. The chair sits facing the fire. Sam can almost see Dean sitting in the chair staring into the fire. Sam was sure the bed was just for fucking. His mind was whirling with the thoughts of how many other demon’s or souls Dean has been fucking since he turned. He knows Dean’s appetite is huge and it can only get worse as a Demon with no inhibitions. Sam begins to wonder what he can expect out of his Demon brother. Could he even hope for love? He is just going to focus on Dean and hope his torture isn’t too long. He needs Dean but how will it be when they are both Demons? 

“What is going on here?” A cold booming voice interrupts Sam’s thought. He turns to see Dean shirt off, in jeans, boots, and obviously angry. 

“Good to see you too Dean. I brought Sam here to be your slave. It is your job now to turn him into a Demon.” Crowley uses an even colder voice and turns walking to the door. He snaps his fingers right before the door and vanishes.

“Well, well Sammy. I’ve got to know why?” Dean doesn’t look really interested in the answer. He seems to be eyeing Sam as if he was a starving dog looking at a steak.

“You’re all I’ve got Dean. You don’t care about anything, but I thought you might still enjoy torture. What do you care anyway?” Sam was trying to fight back the panic in his mind. He doesn’t know what this Dean is capable of.

“Trust me I don’t. This is going to be fun! First things, first. We need some equipment.” Dean turns to the wall next to the fireplace and snaps his fingers. A large iron X appears on the walls covered in chains. There are dark spots that look like blood, but Sam tries not to think of it. Then Dean snaps again making a large wardrobe of dark cherry wood appear a few feet away. He struts over to it and opens it to show Sam all the different torture and BDSM devices stored inside. The firelight makes deep shadows in the wardrobe. There are whips of all shapes and sizes. Some dildo’s that look way too large. There are a few knives that make Sam worry. There are more things he has no idea what are. Sam is not a prude. He has not ever spent much time looking into these kinds of sex items. Sam notices a twitching in Dean’s tight jeans, and it makes him shiver. Even in the middle of his fear he is reacting to Dean’s cock. He looks away quickly, hoping Dean won’t notice.

“You still want this cock?” Dean grins and strokes himself through the jeans outlining his growing dick. He licks his lips as he looks down and sees Sam is enjoying this a little too. Sam hadn’t thought about what to wear that day. He has on his jogging pants and a t-shirt. He had thought up the idea while running. Dean walks to Sam like a predatory cat and pulls Sam’s head down for a hot kiss. While Sam is lost in the kiss Dean reaches around and pulls Sam’s ass towards him so their groins are mashing together. They each moan as they get friction for a moment. The roughness of the jeans feel wonderful to Sam through his soft pants. The feel of Dean’s hard cock so close beyond that layer of cloth make him harder. Dean steps back quickly and pinches one of Sam’s nipples through his shirt.

“You are an eager fuck boy!” Dean laughs and keeps stroking his cock as he watches Sam’s flushed face.

“Please Dean, I need your cock. I have missed you so much, I love you.” Sam was so happy for a moment. Then a cruel laugh from Dean brings his mind back to the present situation.

“I believe the cock part, but you don’t love ME?! I am not your Dean. I want to fuck you believe me. You just need to understand the rules.” Dean reaches out again and grabs Sam’s hair tight in one fist and turns to walk towards the X on the wall. Sam cries out and walks along with him, so his hair isn’t pulled out. Dean used to pull Sam’s hair during sex, but this has no restraint behind it. Dean would pull out his hair if he didn’t follow. Sam lets one tear fall and shivers as Dean shoves his chest into the iron X. He hears a snap and realizes he is naked. Sam instinctively moves to cover himself when he feels a hard smack on his arm.

“No, you don’t do anything without permission. Spread out your arms and legs and hold still!” Dean’s voice is cold and commanding. Sam just complies feeling more tears flowing. He can’t help but mourn what they had. He knows now it will never be possible again. Dean gets his arms chained to the X and then walks away. Sam turns his head looking for him and receives a hard smack to this thigh. He screams.

“You will hold still or else this will be much more painful. I like that but you won’t. First rule is don’t speak unless I ask you to. I don’t want to hear anything out of you but screams and moans. Second rule is, obey my commands immediately.” Dean walks to the side to see Sam’s face and smiles even wider at the tears.

“Aww is the big baby sad? Poor little Sammy.” Dean laughs loudly at the horror on Sam’s face. His voice is so cold.

“You will learn there is nothing human about me. I remember being human, but I don’t care. You are a distraction. I know Crowley. He wants to gain back his power and needs me out of his hair. Be entertaining and you will stay.” Dean reaches out and brushes the hair out of Sam’s face then holds out his hand under Sam’s chin.

“Spit.” Sam spits as much as he can and then listens to Dean’s footsteps as he walks behind him. He hears the rasping sounds of clothes being removed. He shivers waiting for the pain. He feels something cold and metal rubbing up against his asshole. He jerks away and receives a hard smack to his ass. He cries out and then holds still even though his muscles are quivering. He is biting his lip. Dean laughs and this time twists as he inserts what feels like a metal tube inside Sam. It hurts but he adjusts easily. It is smaller than Dean’s cock, so it isn’t so bad. He is glad he spit enough because it is shoved harshly as far as it can go inside him. He cries out and is rewarded with a moan from Dean. He begins to scream when the tube is shoved in and out of his tender hole fast and deep. There is a ridge on the tube that begins to rub over his prostate, and he bucks back into the device. That gets him another hard smack.

“Hold still!!” Dean is panting hard and Sam thinks he may be jerking himself off as he fucks Sam. The thought itself makes Sam come immediately all over the iron X. He is shivering and floating down from the orgasm when he feels a tearing of his skin across his back. He screams so loud his throat feels like it is bleeding. He feels a trickle of blood down his back as he pants trying to get himself under control.

“Fuck boys don’t come first!” Dean sounds amused and the device is removed. Dean pushes himself inside Sam in one stroke burying himself to the hilt. Sam gasps and shivers. Dean is so thick and it fills him up. Sam closes his eyes trying to picture them in the bunker making love.

“Now you will make me come.” Dean’s voice is so low and full of heat it makes Sam shiver. Dean bites down on Sam’s back not too hard but hard enough to make him wiggle. Dean licks up the blood trickling down his back. Sam pushes back against Dean and tries his best to make Dean come quickly. Dean’s breathing gets harsher and he begins to shove Sam hard against the X. He is pounding inside Sam so hard that Sam is using all his strength to keep from hurting himself against the metal of the X. He is in pain and just wants this to end. As soon as he moans in pain Dean comes violently inside him. Sam gasps at the feeling of being coated inside. Then when Dean pulls out something else is shoved inside him.

“Good fuck boy. Now this plug is there to keep my come inside. If you let that plug fall out, I will whip you again. My barbed whip seems to work the best.” Dean’s voice is like a purr of satisfaction. He walks away and shuts a door firmly behind him. There is a jingle of a key in a lock and then silence.

Sam is crying he had been enjoying this until the pain of the whip. He knew this would be torture. He loves Dean so much. That is why his heart is breaking. He can’t have his love without this pain. He feels like part of his soul is drying up like a dying flower. He isn’t sure how a demon soul is made. He is not sure how much torture it will take. Sam needs Dean so if this is the way to keep him, he will do anything. 

A few hours later Sam jolts awake from the sound of a door flying open. He turns his head expecting Dean, but he sees a demon he doesn’t know grinning at him. Sam doesn’t know what to do. 

“Looky what we got here. A naked and tied up Winchester. I didn’t believe the rumors. You may not recognize me Sam, but I know you. It doesn’t matter anyway.” The demon is walking towards him unbuckling its pants. His grin makes Sam cold all over. He has no way to defend himself. He also doesn’t know if Dean sent him. What if he is to be tortured by others for Dean’s amusement? He doesn’t see Dean though.

“Don’t do this. If Dean finds you…” Sam doesn’t know what Dean would do. He is a demon now.

“Dean is not as smart as he thinks he is. He was the one that bragged about you being here.” The demon is close enough to run a finger along Sam’s arm. Sam moves away as far as his chains will go. His heart is beating so fast. Then it hits him his legs are free. Sam lets the demon get right behind him. As soon as the demon touches his ass Sam puts his weight on his left leg and uses his right leg to kick behind him right against the demon’s knee. He hears a crunching sound and a scream. Sam grins and shifts to go after the other knee when he hears a roar from the doorway. Turning his head, he sees Dean and he almost laughs. This demon is fucking dead.

“What the FUCK are you doing Clark?” Dean is already walking towards the demon on the ground. He is panting and growling.

“Dean look I just wanted to play a little. He fucking broke my knee.” Clark is trying to crawl away from Sam as fast as he can.

“I knew one of you would be stupid. HE.IS.MINE.” Dean reaches Clark and lifts his injured leg up in a jerking motion. Clark screams louder as his knee is pulled out of joint. Dean smiles coldly as he begins to drag Clark from the room. Sam is doing his best to hold in vomit. This was savage for Dean and he must remind himself this is Demon Dean. He is shivering and listening for even worse sounds. Is this really his Dean anymore? He must remember he won’t be himself either by the end of this. The question is can he make the journey? He doesn’t hear Dean come back. He only feels a sharp stinging on his back and gasps.

“You dropped the plug fuck boy.” Dean growls at Sam before reigning more blows all over his back. Sam groans and quietly lets tears fall. 

“I’m sorry Dean.” Sam’s breath hitches and he waits for more pain.

“You are not sorry yet. Don’t call me Dean. I am your master.” Dean reaches around and gives Sam’s limp cock a squeeze.

“This is mine. No one will every touch you but me. Don’t ever speak again unless I ask fuck boy.” Dean’s voice has a strange note to it. Almost as if he loves Sam. 

“Yes master.” Sam speaks the words as if he is saying I love you. Sam feels the sting of another blow to his back.

“Good fuck boy.” Dean looks into Sam’s eyes studying him.

“You will rest and heal up for me. I need a clean fuck boy.” Dean unlocks Sam’s chains and sits him on a blanket on the floor. Dean puts cuffs on Sam over some cloth to keep his skin from chaffing. He puts a bowl of warm water, soap, and towels next to Sam.

“Clean yourself and rest. If you are good next time you will be fed.” Dean runs his fingers through Sam’s hair absently and walks to his bed by the door. He sits watching Sam go about cleaning himself up. Sam glances at Dean briefly from time to time. He feels like there is still some humanity in Dean. Maybe Dean loves him still. He must work on a way to test this without getting punished too much. Maybe this is just a fantasy Sam has, to hold on to his sanity. He needs Dean and he must know if his Dean is still there.


	2. Day 2

**Summary for the Chapter:**

> Sam is at Dean's mercy and he is learning to enjoy himself.

The next morning Sam is rudely awoken. A cold bucket of water is dumped over his head. He spits out the water and sits up as he hears harsh laughter. Sam turns his head and glares at Dean. Dean’s laughter cuts off and his face shifts to anger. He stalks towards Sam and picks him up under his arms lifting him up to his feet in one swift motion. Dean pulls Sam’s face right to his.

“You will learn to obey today fuck boy!” Dean turns Sam towards the bed and throws him face first onto the bed. Sam is draped across the bed his legs hanging off. His face is up against a silky pair of boxers and he has a moment to wonder if they are Dean’s before a stinging pain shoots across his thighs. Sam cries out in pain and wiggles as if he could crawl away.

“Hold still. I will add an extra hit of the cane for each movement.” Dean’s voice is commanding but not angry. Sam hopes he will be able to hold still.

Dean uses the cane and taps it gently over Sam’s skin moving up and down his legs. He seems to be testing each area for sensitivity. When Sam sucks in air as the cane taps on his calves suddenly Dean stops. Sam holds himself rigid waiting for the blow. When he hears nothing, he starts to relax. The cane comes down on his calves with a whistling sound. Sam screams again and can’t help but pull up his legs. This was a mistake that Sam didn’t realize until too late. The cane comes down on the bottom of his feet that are now up in the air. He screams again and lowers the legs. Dean chuckles evilly.

“Two extra hits so far fuck boy. Move like that again and I will restrain you.” The glee in Dean’s voice makes Sam moan. He wonders if he is beginning to enjoy this.   
Dean goes back to gently tapping the cane over his legs. Sam manages to hold still and not make a sound. Dean starts hitting the cane a little harder on Sam’s butt. Sam groans but manages not to move. He is getting so hard and he is thinking of wiggling just to get more hits. Dean hits the cane against each cheek separately harder each blow. By the time Sam’s butt is turning red they both are breathing heavy. Dean snaps and Sam feels a hot hard cock on his red skin. Dean must be naked now. Sam moans deep and low in his throat. 

“So hot fuck boy.” Dean’s voice is full of heat and he rubs a hand over Sam’s hot skin. Sam hears Dean jerking his cock and hears spitting. Then Deans fingers are rubbing spit over Sam’s hole. 

Sam can’t help it he humps the bed a little. The fingers are removed, and a sharp stinging smack makes Sam cry out. Then the fingers return, and he holds still as they slide inside. He moans but it does hurt as the only lube is spit. Dean’s speed of jerking and his fingers speed up then he adds another finger spitting on Sam’s hole. They are both moaning, and Sam’s hard cock is trapped between his stomach and the bed. It is torture not to be able to touch himself. Dean gets four fingers in and Sam’s moans turn to grunts of pain. He is beginning to think Dean will be trying to get more than fingers inside him.

As Sam starts to cry out from the stretching of Dean’s fingers, he hears Dean grunt and warm wet liquid is coating his hot skin. He groans loving that Dean came all over him, but he begins to be concerned when the fingers don’t exit his hole. He feels the cum being rubbed on his hole. Then the surprise of his life as Dean’s fist begins to enter him. The knuckles get in and Sam screams he has never felt so full before. Dean is already moaning again and even through the pain that sound of Dean moaning and being so full Sam comes untouched all over the bed. The pain he feels along with the pleasure is a new level of enjoyment. Sam is beginning to wonder if he is already losing his humanity.   
“Such an eager fuck boy. You made a mess. At least you remembered the first lesson. You don’t come first. I think you have earned breakfast. First you need to lick up all that mess you made.” Dean walks back and watches as Sam nods and scoots backwards. Sam bends down and licks at the clothes and sheets. Sam doesn’t mind the come but he doesn’t like licking it off the clothes. He does his best then uses his fingers to scoop up any left on his skin and sucks that off his fingers. His eyes close and he enjoys thinking of Dean’s cock in his mouth.

“Good job. Now sit on your pallet and then you can eat.” Sam nods and goes to his bed sitting and seeing a plate of fruit and cheese with a few pieces of bread and a glass of water. He is hoping this was Dean remembering what he likes and trying at least a little to be kind. Dean pats Sam on the head like a good boy. Sam begins to shiver he is getting cold being naked all the time. The fire doesn’t heat up the whole room. Dean squats down in front of Sam.

“You are being good for now. I will grant you some clothes. I won’t need you to be naked for our later activities.” Dean’s eyes are practically glowing as he watches Sam eat. Sam gets uneasy as he eats because the more he eats, the more Dean’s eyes sparkle. Sam concentrates on eating and ignores Dean. When he is done, he feels sleepy and begins to nod off. He doesn’t even realize when he falls asleep. 

Sam comes awake from a dream about drowning and he is panicking as his eyes open. He realizes his mouth is full of Dean’s cock and it Is shoved far enough in he can’t breathe. He looks into Dean’s eyes. Dean reaches down and grabs Sam by the hair pulling him off his thick cock. As soon as he can Sam draws a huge breath and pants trying to calm himself. Dean watches him his cock bobbing in front of Sam’s face. Sam moans and sinks himself down on Dean’s cock. He has wanted to suck Dean off for so long. Sam goes all the way down on Dean swallowing him down and gagging a little. He learned how much Dean loves the sound and the spit that drips down his chin when he pulls back. Demon Dean loves this even more. Dean moans and his cock jumps in Sam’s mouth. Sam hums around the cock and bobs a little faster. Sam’s cock is hard so fast and there is an extra jolt of resistance and a little pain. He realizes he is dressed but also there is a restraint around his cock. Before he can think anything else, Dean shoves his cock in all the way and then holds on to Sam’s head holding him down. Sam needs to breathe. Sam is panicking again because he doesn’t know how to get away. Dean is strong and he can’t fight to get away. He also realizes he is in cuffs on his wrists and ankles so he can’t do anything. His vision is going grey and he feels himself passing out. Suddenly he can breathe, and Dean is smacking his face hard. He jolts into a sitting position panting. He looks up at Dean and realizes that Dean has come all over his face. He feels the liquid and moans because he loves Dean’s come.

“What a good fuck boy. I love the look of my come on your face. You are dressed but there is a cage around your balls and cock. You can get hard, but it will hurt. You won’t come until I am satisfied with your progress. For now, you need your sleep. We have a lot to do.” Dean winks at Sam and lets him wiggle to lay on his pallet on the floor. Sam watches him go to the fire and sit looking in the flames. He drifts off to sleep with that sight. His dreams are darker now and he is wandering lost and scared. Is that his human soul lost in the pain? Even in his dream Sam can feel his soul changing.


	3. Dean's Plan

**Summary for the Chapter:**

> Dean has a plan. Sam is changing and Dean wants to move things along.

**Notes for the Chapter:**

> This will end with chapter 4 and that will be soon. Thanks for continuing to read this.

Sam has no idea how long this has been going on. He hasn’t seen daylight so he can’t tell the passing of days. He thinks it must have been a few weeks. Sam knows he is changing. He hasn’t cried since the first few days. He doesn’t feel as many emotions. When he sees Dean, he still feels love. He feels just as much lust as love and wonders if that may be how a demon feels love. He has been thinking about his soul a lot lately when he has time to himself. His tolerance for pain has gotten much higher. This has been making Dean a little aggravated. Sam is not sure, but it might be why Dean has started being around less. He has had more time to think in the last day or so. A few slave human souls have brought him his food when Dean isn’t here. He tries to talk to them, but they are terrified. He thinks Dean must have threatened them. This is what makes Sam hope that Dean still loves him. He is so possessive and protective and that has been the start of their love in their lives. It had grown from just protecting Sam to them realizing they were in love and acting on that. As Sam was musing on the first time they fucked Dean comes in with a very evil smile on his face.

“Today fuck boy we are going to start an experiment. I have a plan. Eat now and nap I need to set something up.” Dean leaves food for Sam and stalks back out the door.  
Sam eats quickly and falls asleep. He is not sure what is going to happen, but he is feeling fear like he hasn’t felt in a while. The scary thought that Sam now looks forward to fear is what he falls asleep to. Jingling chains is a normal sound for Sam, but the hydraulic sound is what makes his eyes open. He looks over on the wall and sees chains but also what looks like a padded black chair. It can be raised or lowered and that was the sound he heard. The chair is strange. It has a place for each leg to be shackled to, and his butt was hanging through a gap. The legs are a big V and the back is just a straight padded back. He is staring at it mouth open when he feels a stinging prickle on his foot. He yells and jerks his leg in. Dean has a small electric prod. Sam has never seen that before and it was not fun. Dean smiles big at the new reaction and Sam sighs this is making his Dean happy. 

“On your feet. Get over to the chair and sit.” Dean watches Sam eagerly get up and hurry over to the chair. He had stopped chaining Sam up when he was alone. Sam wasn’t going anywhere, and Dean knew it. Sam gets on it and settles in. Dean chains his arms in a t position to the wall and cuffs his ankles to the chair. Sam wiggles in excitement. Dean chuckles and his smile almost seems warm for a moment.

“You haven’t held my come inside you since the first day. The more you have the faster we can get you to the goal.” Dean then moves the chair up a little farther to make it easier. He is already hard, and the sight of his hard cock makes Sam hard in an instant. Dean grins at Sam’s cock and gets out a small flogger.

“Fuck boy’s need to control their cock.” With a grin he starts to use the small flogger on Sam’s cock. Sam gasps at the first hit. He wiggles but can’t move much. Dean smiles and hits a little harder. Sam cries out and his cock begins to deflate a little. Dean hadn’t seen that happen in response to pain before. He files that away for later use. He gets the cock cage and locks up Sam’s to keep him from coming. Sam hates the cage but knows that a good fucking from Dean will follow it. Sam screams as he gets shocked again. Dean laughs loving his response to the prod. He goes to Sam’s feet and begins by shocking his feet as Sam wiggles and yells. Sam’s feet are his worst place for anything to happen. They are so sensitive, and Dean uses that when he wants Sam to pay attention. He moves up Sam’s leg with shocks all over and Sam is yelling with every shock. 

“Please Master Stop!!” Sam yells out after Dean gets to his chest with the shocks. He gasps realizing he broke a rule. He watches Dean’s face go from amused to cold.

“You know better. I think we need a new punishment. NEVER interrupt me fuck boy!” Dean snaps and a candle appears in his hand. It is lit and Sam is not sure what is coming next. He wants to say he is sorry but that might make things worse. He shivers in fear waiting for what is to come.

Dean looks in the candle and smiles. He walks to Sam’s legs and tips the candle a little so some of the wax runs out and drips on Sam’s shins. Sam yells when it touches his skin. It stings but doesn’t hurt too much. He likes it better than the shocking. He figures if he reacts worse maybe Dean will keep this up instead. Sam starts wiggling and crying out in pain more and more. Dean smiles and moves to the other leg waiting for more wax to build up. Unfortunately, Sam’s cock betrays him and starts to harden again. 

“Fuck boy likes the wax. Good to know. You might not like it here though.” Dean moves the candle to right above Sam’s nipple. He drips the wax and Sam yells again, but it turns to a moan. His cock is pushed against the cage and the pain is building. It is ok for Sam because it will keep him from coming and that punishment would not be fun.  
Dean moans and rubs his hard-bobbing cock. Sam groans and gasps as his hard cock pushes harder against the cage. Dean snaps getting a bottle of lube. They had moved to lube, so they didn’t have to heal up Sam in between fucking. Dean dribbles it on his cock and rubs it on. He positions himself between Sam’s legs and in one swift flick of his hips is buried fully inside Sam. They both moan together. Dean starts fucking Sam with slow teasing strokes. He pulls almost all the way out before slamming home. Dean looks into Sam’s eyes as he keeps the slow pace. Dean bites his plump bottom lip trying to hold off his orgasm. He reaches over and peels off the wax on Sam’s nipple. Sam gasps but loved the feeling. Dean groans again and stops. He snaps and gets a cock ring putting it on. He wants to build up enough come to really fill Sam up, so he needs to hold himself off. Once the ring is on Dean resumes his slow pace and his eyes are full of fire. Sam doesn’t know if he will be able to hold off. The cage is still painful but seeing Dean’s eyes make him want to come. He is pulling on his chains wanting to reach out and touch Dean. Dean watches Sam and knows exactly what is going on. He grins at Sam again as he slams home. He reaches up and puts a hand around Sam’s throat. He only squeezes a little cutting off Sam’s breath just enough to make Sam feel floaty. Dean speeds up the pace a little as he watches Sam’s face. When he sees Sam’s eyes close a little he lets go and Sam gasps. Dean picks up the pace again and then grabs Sam’s throat and squeezes a little harder as he starts to pound into Sam grunting. He looks into Sam’s eyes and whispers “I love you” before coming violently and letting go of Sam’s throat. As he pulses inside Sam, he feels a warm liquid dripping on his stomach. He looks up and sees Sam’s cock still spurting his come. Sam had not passed out, but his eyes were closed. Dean pulls out and puts a plug inside Sam and uses some rope and the rings on the sides of the metal plug to tie them to Sam’s legs. 

“Good fuck boy. This should stay inside no matter what. I guess you need something besides that cage, but you did wait until after I came.” Dean gives a light bite on Sam’s thigh before removing the cage from his cock. He lowers Sam’s chair down a little. Sam still hasn’t opened his eyes, so Dean cleans himself and leaves.

Sam can’t believe Dean said he loved him. What does that mean? He wanted Sam to know or was it a tease to get Sam to come. He can only hope it was the truth. Maybe all this would be worth it. He slips off to sleep with a grin and a peace he hasn’t felt before. His dreams are a writhing mass of dark snakes holding him and rubbing all over his skin. He is not disgusted at all and loves the feeling of the cool smooth bodies rubbing on his skin. He had not liked snakes before, so this made him wonder what it meant. He feels a little pain and gasps. Did they bite him? Then he feels a little numbness and it makes him shiver.

Dean is sitting in his chair before the fire listening to Sam’s sleeping sounds. He feels the darkness inside Sam’s soul building up. His tolerance for pain and how much it makes him horny is surprising. Dean has had to dig for more and more torture things that won’t be too intense. He feels the need to protect Sam and he really does love him. He doesn’t have feelings like he used to, but this is a part of him nothing could burn away. He just hopes that Sam will still love him when he is demonized. If he can Sam can. He starts to think of how Sam came here, and he smiles. He hears the jingling of chains and decides to fill Sam again. He knows that the come inside Sam will hurry along his change. He had to research it but the more of himself he gets in Sam the more it will take over Sam and help the change. He puts on his master face and stands up headed to his chained-up Sammy.


	4. Demon Brothers

**Summary for the Chapter:**

> Sam is finally ready to see if he is finished changing. They are both ready for this new chapter in their lives.

It has been two months that Sam has been in Hell with Dean. They have tried so many kinds of play and as Sam’s soul changes even more they have gone to extremes. Dean pumped Sam so full of come he was surprised it wasn’t dripping out of his nose. He held it in and it slowly worked it’s way into every fiber of his being. He felt calmer all the time. He had emotions so he wasn’t sure if he was progressing enough yet. He didn’t worry about what Dean did anymore. Dean’s favorite thing now is to restrict Sam’s ability to move or see. Last night they decided to try a new kink. When dean brought in what looked like a black diving suit and a lot of tubes Sam was curious. He wasn’t afraid of anything anymore. Sam is sure he is close to full demon now but it doesn’t concern him either anymore. Their life of play has become all he thinks about. 

“This is a rubber immersion suit. The tubes are so that you can still breathe and let out things as well. Luckily I am a demon so this will be much easier than for everyone else.” Dean snaps and tubes are coming out of Sam’s nose, mouth, and urethra. The stomach tube was weird but ok. He was more excited than worried. Sam was surprised Dean didn’t bother with a tube in his ass. He knows Dean is still likes having his come in Sam so he figures that is why. Dean puts a gag in Sam’s mouth that the stomach tube threads through. He also puts in ear plugs. Dean snaps and the suit is fitted over Sam’s body without all the pulling and strain that would be needed for everyone else. 

Sam can see nothing at all and hear only louder sounds. He feels like he is wrapped in a cocoon. Almost like the womb. It is warm and cozy and Sam is happy there is a nice rubbery resistance to his hardening cock. It is a nice friction too. Sam tests out his movement in it and finds that he can get some friction but not enough to get off. He moans a little again and wiggles. Dean is watching Sam and gently touching the outside of the suit. He loves to see Sam like this. He is fully at Dean’s mercy and that makes Dean feel satisfied. He has decided to leave Sam in it all night, but he will watch for part of it. After a few hours of moans and wiggles he can tell Sam has fallen asleep. He checks the tubes just to make sure all is well. Then he pokes at Sam and when he finds an erection poking against the suit, he moans himself and gently rubs a hand against it. Sammy hard makes him hard. He starts to rub his cock over Sam’s hard cock. The feel of the rubber against Dean’s cock is amazing. It is friction he loves and against Sam’s cock it makes him come in a few thrusts. He looks at his come covering Sam’s rubber coated cock and grins. This was a great idea. 

When Sam wakes up, he is confused for a moment. He can’t see and there is a lot of tubes. He squirms a bit until he feels a tap on his shoulder. Dean snaps it all away and grins at Sam.

“That was fun for me. Tell me how it felt fuck boy.” Dean gestures to food and water for Sam on his pallet. Sam sits down and drinks a little to compose his thoughts.  
“It was warm and cozy. I slept most of the time. I felt you touching me, but I couldn’t move enough to get off. I am glad it made you happy master.” Sam grins at Dean he feels so relaxed now. Being lost in a world of warm cozy cocoon was very freeing. He also had dreams. He could see things from his life happening and he didn’t care. He thought at the time it was a dream and it was why he wasn’t worried. Now that he thinks back on it, he really doesn’t care. People in his life like Cas, his mom, or dad. They were pictures in a book they didn’t mean much to him. He is sure he is so close now to becoming Demon. He doesn’t even feel the huge excitement he thought he would. He still wants to be with Dean but not for the same reasons he did this. He is so lost in thought Dean kicks his ankle and says his name a few times.

Sam looks up at Dean confused.

“Where were you? I practically had to shout in your face.” Dean watches Sam’s face with a frown. 

“Sorry master. I think my soul is getting close to being full demon. I am having dreams, but I don’t really care about anyone in them. It’s weird. Do you know how we can tell if I am close?” Sam is all curiosity.

“I don’t actually know but I bet we can test it.” Dean’s eyes sparkle as he thinks. Sam has been thinking about this for a while. He wants to see if maybe he can reach out like he used to and control things. Sam closes his eyes and concentrates on the chair in front of the fire. He tries to slide it across the floor, and he hears a squeaking. He opens his eyes in surprise. Dean is doubled over laughing quietly.

“You had your hand out towards it I just had to.” Dean chuckles at Sam’s bitchface.

“Enough of this. I need your services fuck boy.” Sam shivers when he is called by that name. Pleasure will soon follow.

Dean’s eyes are full of lust and his cock is already hard and straining at his jeans. He snaps and a strange round object appears. It looks like a large spool for wires. It is round, wooden, and big enough to strap Sam to the metal shackles along its curves. Sam walks over and looks it over extremely curious. Another snap has him naked and his excitement is obvious. 

“Lay down over the curve with the small of your back.” Sam drapes himself on the smooth wood and puts his hands above his head. He feels Dean attaching his ankles first. It’s cold metal, but Sam loves the feel of metal now. He waits and Dean secures his hands as far away from his body as they can get above his head. Sam feels very stretched out and open to Dean. He moans and his long hard cock bobs. A long string of pre-come is stretching down towards the floor. Dean puts a blindfold on Sam and they both moan. Dean puts a circle gag in Sam’s mouth. It is a ring of metal open in the middle that holds Sam’s mouth open to receive Dean’s cock anytime. This has become a new favorite of Sam. It helps him stay open and deepthroat better. Sam is aching for Deans cock so badly that he wiggles testing the restraints. He listens for Dean’s footsteps as they go to the cabinet and comes back quickly. He first feels the sting of a whip on his stomach. Sam grunts and instinctively tries to curl in on his stomach, but he can’t move. Dean chuckles again and whips Sam’s stomach a few more times watching Sam straining and his cock dripping more. Suddenly a stinging burn starts on his chest. He cries out as this pain is not familiar. He smells a coppery smell and realizes he is bleeding. That is not normal, but he can’t ask what is happening.

“This knife is going to carve my ownership in your hide. You are mine now and forever Sammy.” Dean’s voice is full of lust and he soon make a few more strokes in Sam’s chest. Sam doesn’t know what is carved on him, but he will be proud to have this on him for the rest of his days. Sam feels Dean’s tongue licking up the blood and sealing the cuts. He shivers and feels the need to come. He tries to hold it but when a soft sucking bite on his nipple happens, he comes hard yelling out Dean’s name as ropes of his come shoot out onto himself and the floor. He realizes seconds later that was a mistake.

“Fuck boy! You were very bad, but I have just the punishment for you.” Dean’s voice is cold, but Sam can tell he is excited for this punishment. Sam shivers waiting and suddenly feels something slipping over his softening cock. It feels like a snugger version of a cage. There are openings and something solid that is settled onto the curve of his cock like a spine. He also feels a bar of rubber that settles in the slit on the head of his cock. He is already getting hard but the pain that comes with that is shocking. It is like someone’s hands squeezing his cock. He cries out and hears Dean’s harsh laugh.

“This is what they call the gates of hell. It is a new kind of restraint for your very naughty cock. If this doesn’t work, we will have to put something on those naughty balls too.” Dean starts to shock Sam’s feet and Sam shrieks and tries to move away but he can go nowhere. The shocks start coming up his legs and his stomach. Sam is screaming and moving all the time. The restraint is painful and makes every movement of his cock bad. 

Sam pants when he feels Dean move away then little stings are raining down on his chest. It is the heavy cat o nine tails. Sam’s least favorite toy. It isn’t barbed but the weight when it hits is painful. Sam gasps as he feels it hit a thigh and then the other. Dean’s swing is heavy, and the hits are more painful than he remembers from before. Sam tries with all his strength to get away and he hears some creaking, but nothing was budging. 

Dean goes back to Sam’s chest and the blows are getting lighter and when they graze over Sam’s nipples, he feels like they are on fire. That makes him moan and that stops Dean. He wants to fuck Sam, but this position only goes well with face fucking. Dean straddles Sam’s chest and scoops up Sam’s drool from his chin and chest and rubs his cock before slipping it inside the ring in Sam’s mouth. Dean’s cock is thick, so it is a little tight but not bad. He slides all the way down to the root. Sam is making gargling noises and Dean pulls out bringing a string of his own pre-come and spit from Sam. He moans and then takes off the circle gag. He needs suction too. 

“Fuck boy will suck me off and do it well or you will spend the night on this restraint.” Dean sinks back in Sam’s mouth and is rewarded with greedy sucking and slurping. Sam knows how to use suction well and he loves sucking Dean’s cock. Dean begins to fuck Sam’s face with an increasing speed. Sam is groaning and moving his head up to take dean deeper. Sam loves to be face fucked. He feels light headed when Dean stays deep in his throat for too long. Dean holds Sam’s head in his hands as he goes deep and holds Sam on his cock. He loves the feel of Sam’s throat spasms when he needs air. Dean pulls out when he feels Sam about to pass out. He lets Sam catch his breath before doing it again and this second Sam uses his teeth on Dean’s cock, Dean comes hard down Sam’s throat. Sam moans and Dean pulls out to let Sam breath. Dean staggers to the bed and sits watching Sam’s body. Sam is so hard and can’t do anything. 

“This restraint is perfect for you fuck boy. It is holding you back. Good you will not come for at least a few hours.” Dean smiles. 

“You were a good fuck boy. I think you need to stay and think about what you did.” Dean pulls of Sam’s blindfold and Sam looks at his chest. He gasps when he sees what is on his chest. He is surprised and delighted to have his brother’s initials in his chest. He just doesn’t see it as emotionally as he used to. Then it hits Sam. He isn’t hungry. He hasn’t felt thirsty or hungry in a while. He hasn’t refused anything from Dean, but he is realizing his body doesn’t need those things. 

“Wait Master! I think I may have come to the end of my journey!!” Sam is so enthusiastic he doesn’t bother to wait for permission to speak. The whip to his legs makes him gasp but it is also not as bad as Dean can dish out.

“Ok, tell me why.” Dean whipped him out of habit, but he has a little spark of excitement.

“I am not hungry.” Sam says it with such pride that Dean immediately laughs at him.

“Uh that’s it? Really?” Dean is pretty sure now that Sam is right, but he wants to make sure.

“Master, I have been hungry since I got here and until a few days ago I needed the food. Now I feel different. I can eat it, and everything is fine, but I do it out of habit now. Does that make sense?” Sam is trying to come up with more indications, but he can’t.

“Sammy you are at least mostly demon then. When I first turned, I ate and drank because I could, not because I needed to. It was like a habit I couldn’t break. That was the first thing that hit me that I was a demon. I think getting Crowley in here will help us find any other methods of testing.” Dean was very excited and snapped himself to Crowley.

“Hey Crowley! I think Sam is ready. I just don’t know how to test him.” Dean is beaming and hopes Crowley won’t be too much of a dick.

“Hello Squirrel. I think I can pop by for a moment.” Crowley is hoping this is true but also afraid of what will come next.

When Crowley and Dean get back Sam is alert and almost shivering with the need to know. Crowley smiles at Sam’s bondage.

“I see you two have been playing. How nice. Can the moose be a little more clothed?” Crowley looks away for a minute pretending to study the firelight.

Dean snaps and Sam is out of his restraint and clothed. Sam sighs at the feeling of being clothed again. He can still feel the cock restraint and that makes him horny, but he has to hold off on that.

“Better, now I am not sure what powers he will have so we need to go through a few things first to see. First things, first Sam can you feel any surges of electricity like power inside. It might feel like a bubble or a wave of energy.” Crowley looks calm as usual but he is kind of excited too.

“I have been feeling that but I wasn’t sure what it meant..” Sam is almost quivering.

“Ok well I want you to reach out to that energy and focus on it. Like a blanket I want you to grab ahold of it and pull it over you like a coat or a blanket.” Crowley watches sweating a little. How powerful is Sam?

Sam closes his eyes and focuses on it. Once his mind grabs it, he finds it easy to let it take over. When he opens his eyes Dean and Crowley both are staring with their mouths open. Sam can see but it is different. He can see power now too. He can tell Crowley is powerful with a very red glow about him. Dean is more of a blueish color of cold. The energies swirl around them like fog in a wind. He can also finally see Crowley’s true face. It doesn’t distress him and that is when he is sure he is no longer human. Dean has another face but to Sam it looks as beautiful as his normal one. Sam smiles and laughs.

“I am demon. I can see your true faces and I can see your power. I can’t believe it.” Sam is almost bowled over with this fact. He would have cried if he had been human for all the lost possibilities of his life. He is just satisfied now.

“Alright Moose Congratulations. When you pulled on your power, I could see your true face too, but it isn’t fully formed so you have a little more to go. The second thing is can you reach out with the power to control other things?” Crowley is curious how much is going on inside Sam.

Sam nods and reaches out towards Dean, this is what interests him most. He tries to remove Dean’s clothes. He frowns as the power seems to slide across Dean but not get hold. He puts out his hand and when he does, he imagines Dean’s clothes gone and feels a snap inside as he pulls the power back. He opens his eyes and sees a very surprised and naked Dean. He can also see just how excited Dean seems to be about this.

“Well you don’t need me right now I am off.” Crowley snaps his way out and back to his throne. He has made a lot of progress while Sam and Dean were holed up together. Now that Sam is a demon what will they do? They won’t be hunters of course but what else can they do. Maybe they will take longer fucking each other and forget about the rest of hell. He will need to get a spy near them soon so he can keep tabs. 

When Crowley is gone Sam and Dean walk towards each and before Sam gets to Dean his clothes are already off. Sam smiles and reaches out to touch Dean. He hasn’t had the ability to for a while. Sam pinches one of Dean’s nipples and rolls it pulling it as far as it will go. Dean groans and runs his fingers through Sam’s hair. Dean is so full of lust he can’t stop himself from pulling Sam down for a very deep and passionate kiss. Their power swirls around them. Sam feels a tingling of his skin as if there is electricity close by. He moans as his restrained cock rubs up against Dean’s hip. Dean snaps it away and reaches down to run his fingers over the hot velvety skin. Sam’s cock jumps in his hand and Sam groans again loving the feel of Dean’s hand. Sam closes his eyes enjoying Dean’s hand job. He hears a snap and Sam opens his eyes to see Dean holding a knife towards him.  
“I carved into you but now it is your turn. I want your mark on me.” Sam takes the knife and Dean releases his cock. Dean runs his fingers over the carving on Sam’s chest still with scabs and sore. Sam watches Dean’s fingers and realizes why the carving looks familiar. It was what they carved into the back of the Impala as children. If he was human, he would have wept but now he just admires how well Dean carved it. He will do his carving on Dean’s chest and they will be bonded forever. Sam uses the knife like he did as a child. In his fist like a fork he makes swift movements and Dean just watches not even flinching. When he is done Sam licks the blood like Dean did and bites the nipple just below the carving. Getting a groan from Dean and a smack on his ass. Sam moans as his cock rubs up against Dean’s stomach. He reaches down and strokes Dean’s thick cock feeling its weight and wanting it deep inside him. 

Dean knows and pushes him back on the bed. He snaps a bottle of lube and works two fingers as quickly as possible in Sam before bending him in half, his knees by his ears, and slips deep inside Sam. Once seated he bites Sam’s calf and then sets a brutal fast pace slamming inside Sam his hands holding Sam’s knees. Sam is groaning and screaming with each thrust it is amazing how much pain and pleasure are the same for Sam now. He doesn’t even realize he is coming until he feels the wetness on his chest and a groan from Dean as he immediately follows Sam and coats Sam’s insides. Dean lays over on his side pulling Sam into being the little spoon on his bed. They are almost glowing with the satiated feeling of being together. Dean has snapped a plug and puts it inside Sam.

“I don’t think we need to but I love the thought of my come inside you. I won’t keep you to the old rules. You are mine and we will play but you are not being punished anymore. Whatever shall we do with this eternity together?” Dean is grinning his mind running a few hundred miles per hour. 

“I think a lot more fucking and then maybe we can be bothered with the outside world. The demon Winchesters unleashed upon the world sounds like fun to me. We have work to do.” Sam grins before biting Deans lip hard enough to draw a small drop of blood. Dean licks it up and moans.

**Notes for the Chapter:**

> I hope you enjoyed this tale. If I have enough interest I will start a series about the brothers as Demon's. Please let me know if you would like to see that. Thanks again for following this story.


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